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It is a source of cisoid butadiene for Diels-Alder reactions. This chemical is also a convenient source of sulfur dioxide. It is a solvent used in the petrochemical industry for the extraction of aromatics from hydrocarbon streams.
Thomas E. SampleJr.; and Lewis F. Hatch. 3-Sulfolene: A butadiene source for a Diels-Alder synthesis: An undergraduate laboratory experiment. J. Chem. Educ. 1968, 45 (1), 55.
Hans-Joachim Lehmler. Synthesis of environmentally relevant fluorinated surfactantsa review. Chemosphere. 2005, 58 (11), 1471-1496.
Convenient crystalline source of 1,3-butadiene, which is generated on heating to about 110oC: Rec. Trav. Chim., 61, 785 (1942). For an example of its use in the Diels-Alder reaction, see: Org. Synth. Coll., 6, 454 (1988).
Also behaves as a dienophile in with reactive dienes, for example 1,3-Diphenylisobenzofuran, L00101: J. Org. Chem., 34, 538 (1969).
In the presence of Pd(OAc)2, couples with aryldiazonium fluoroborates to give 3-aryl-4-sulfolenes which are readily isomerized with triethylamine to the 3-aryl-3-sulfolenes, providing a source of the corresponding 2-arylbutadienes: Synth. Commun., 26, 231 (1996).
Lithiation occurs at the 2-position; subsequent alkylation and thermal extrusion of SO2 gave a polyene intermediate in a synthesis of the taxane ring system: J. Org. Chem., 62, 2957 (1997).
Gefahrenhinweise (EU): H303-H318
May be harmful if swallowed. Causes serious eye damage.
Wear eye/face protection. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.